Afleveringen

  • Dylan Field is the co-founder and CEO of Figma, the collaborative design platform that has revolutionized how product teams work. In my first-ever live podcast, recorded at Figma Config, Dylan and I dig into:

    • How intuition and product taste drive Dylan’s decision-making

    • The challenge of keeping things simple

    • Dylan’s thoughts on the future of product management

    • Lessons from Figma’s early days

    • How Figma built their initial user base

    • Dylan’s journey from intern to CEO of a 1,000+-person company

    • The future of design tools and AI

    —

    Brought to you by:

    • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

    • Anvil—The fastest way to build software for documents

    • User Testing—Human understanding. Human experiences.

    —

    Find the transcript at: https://www.lennysnewsletter.com/p/dylan-field-live-at-config

    —

    Where to find Dylan Field:

    • X: https://x.com/zoink?lang=en

    • LinkedIn: https://www.linkedin.com/in/dylanfield/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Introduction

    (01:11) Welcoming Dylan Field

    (02:36) Highlights and surprises from Config

    (06:58) The philosophy of design

    (08:01) Raccoon feet and muffin hands

    (09:57) Building and refining intuition and product taste

    (12:50) How to influence leadership

    (16:14) The role of product managers

    (21:12) The future of product management

    (22:20) The importance of simplicity in design

    (26:10) The long road to Figma’s launch

    (27:44) Advice for aspiring entrepreneurs

    (29:07) Knowing when it’s time to ship

    (30:39) Early user acquisition strategies

    (35:50) Spotting trends and future innovations

    (39:20) Reflections on leadership and growth

    (43:16) Lightning round

    —

    Referenced:

    • Mihika Kapoor on LinkedIn: https://www.linkedin.com/in/mihikakapoor/

    • Rick Rubin on the Creative Act—60 Minutes: https://www.youtube.com/watch?v=sE1teB5bN-w

    • Figma pages: https://help.figma.com/hc/en-us/articles/360038511293-Create-and-manage-pages

    • Leading through uncertainty: A design-led company—Brian Chesky (Config 2023): https://www.youtube.com/watch?v=Dkfijg7s76o

    • An inside look at how Figma builds product | Yuhki Yamashita (CPO of Figma): https://www.lennysnewsletter.com/p/an-inside-look-at-how-figma-builds

    • Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

    • An inside look at Figma’s unique GTM motion | Claire Butler (first GTM hire): https://www.lennysnewsletter.com/p/an-inside-look-at-figmas-unique-bottom

    • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

    • Nadia Singer on LinkedIn: https://www.linkedin.com/in/nadiasinger/

    • Sho Kuwamoto on LinkedIn: https://www.linkedin.com/in/shokuwamoto/

    • FigJam: https://www.figma.com/figjam/

    • Tim Van Damme on LinkedIn: https://www.linkedin.com/in/tim-van-damme-maxvoltar/

    • Coda: https://coda.io/

    • Shishir Mehrotra on LinkedIn: https://www.linkedin.com/in/shishirmehrotra/

    • Websim: https://websim.ai/

    • eToys.com commercial (from Dylan’s childhood acting career): https://www.youtube.com/watch?v=k3Y92aCmmbU

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Jessica Livingston is a co-founder of Y Combinator, the first and most successful startup accelerator. Y Combinator has funded over 5,000 companies, 200 of which are now unicorns, including Airbnb, Dropbox, DoorDash, Stripe, Coinbase, and Reddit. Jessica played a crucial role in YC’s early success, when she was nicknamed the “social radar” because of her uncanny ability to quickly evaluate people—an essential skill when investing in early-stage startups. She’s also the host of the popular podcast The Social Radars, where she interviews billion-dollar-startup founders, and the author of the acclaimed book Founders at Work, which captures the origin stories of some of today’s most interesting companies. In our conversation, we discuss:

    • How Jessica gained the affectionate title of the “social radar”

    • Why defensive founders are a red flag

    • How to develop your social radar

    • What she looks for in founders during YC interviews

    • How YC’s early inexperience in angel investing led to the batch model

    • Her favorite stories from interviews with Airbnb, Rippling, and more

    • Lessons learned from hosting her own podcast

    • Much more

    —

    Brought to you by:

    • Enterpret—Transform customer feedback into product growth

    • Anvil—The fastest way to build software for documents

    • Vanta—Automate compliance. Simplify security

    —

    Find the transcript at: https://www.lennysnewsletter.com/p/the-social-radar-jessica-livingston

    —

    Where to find Jessica Livingston:

    • X: https://x.com/jesslivingston

    • LinkedIn: https://www.linkedin.com/in/jessicalivingston1/

    • Podcast: https://www.thesocialradars.com/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Jessica’s background

    (02:42) Thoughts on being under-recognized

    (07:52) Jessica’s superpower: the social radar

    (15:11) Evaluating founders: key traits and red flags

    (21:00) The Airbnb story: a lesson in hustle and determination

    (25:57) A YC success story

    (28:26) The importance of earnestness

    (32:45) Confidence vs. defensiveness

    (34:43) Commitment and co-founder disputes

    (37:46) Relentless resourcefulness

    (40:00) Jessica’s social radar: origins and insights

    (43:24) Honing her social radar skills

    (45:44) Conviction and scams: a Y Combinator story

    (46:50) The interview process: challenges and insights

    (48:20) Operationalizing founder evaluation

    (49:38) Advice for building social radar skills

    (52:08) The “Reading the Mind in the Eyes” quiz

    (55:19) Jessica’s podcast: The Social Radars

    (01:00:34) Lessons from podcasting and interviewing

    (01:09:58) Lightning round

    —

    Referenced:

    • Paul Graham’s post about Jessica: https://paulgraham.com/jessica.html

    • Paul Graham on X: https://x.com/paulg

    • Robert Tappan Morris: https://en.wikipedia.org/wiki/Robert_Tappan_Morris

    • Trevor Blackwell on X: https://x.com/tlbtlbtlb

    • Y Combinator: https://www.ycombinator.com/

    • “The Founders” examines the rise and legend of PayPal: https://www.economist.com/culture/2022/02/19/the-founders-examines-the-rise-and-legend-of-paypal

    • Patrick Collison on X: https://x.com/patrickc

    • John Collison on X: https://x.com/collision

    • Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/

    • Nate Blecharczyk on LinkedIn: https://www.linkedin.com/in/blecharczyk/

    • Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/

    • Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/

    • Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad/

    • Zenefits: https://connect.trinet.com/hr-platform

    • Goat: https://www.goat.com/

    • Eddy Lu on LinkedIn: https://www.linkedin.com/in/eddylu/

    • Drew Houston on LinkedIn: https://www.linkedin.com/in/drewhouston/

    • Arash Ferdowsi on LinkedIn: https://www.linkedin.com/in/arashferdowsi/

    • Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups

    •Bitcoin launderer pleads guilty, admits to massive Bitfinex hack: https://www.cnbc.com/2023/08/03/new-york-man-admits-being-original-bitfinex-hacker-during-guilty-plea-in-dc-to-bitcoin-money-laundering.html

    • Paul Graham’s tweet with the facial recognition test: https://x.com/paulg/status/1782875262855663691

    • SmartLess podcast: https://www.smartless.com

    • Jason Bateman on X: https://x.com/batemanjason

    • Will Arnett on X: https://x.com/arnettwill

    • Sean Hayes on X: https://x.com/seanhayes

    • The Social Radars with Tony Xu, Co-Founder & CEO of DoorDash: https://www.ycombinator.com/library/Ja-tony-xu-co-founder-ceo-of-doordash

    • The Social Radars with Brian Chesky: https://www.ycombinator.com/library/JW-brian-chesky-co-founder-ceo-of-airbnb

    • The Social Radars with Patrick and John Collison: https://www.ycombinator.com/library/Kx-patrick-john-collison-co-founders-of-stripe

    • The Social Radars with Brian Armstrong: https://www.ycombinator.com/library/K3-brian-armstrong-co-founder-and-ceo-of-coinbase

    • The Social Radars with Emmett Shear: https://www.ycombinator.com/library/KM-emmett-shear-co-founder-of-twitch

    • The Social Radars with Paul Graham: https://www.ycombinator.com/library/JV-paul-graham-co-founder-of-y-combinator-and-viaweb

    • The Social Radars with Adora Cheung: https://www.ycombinator.com/library/L0-adora-cheung-co-founder-of-homejoy-instalab

    • Founders at Work: Stories of Startups’ Early Days: https://www.amazon.com/Founders-Work-Stories-Startups-Early/dp/1430210788

    • Startup School: https://www.startupschool.org/

    • The Social Radars with Parker Conrad: https://www.ycombinator.com/library/Ky-parker-conrad-founder-of-zenefits-rippling

    • Rippling: https://www.rippling.com/

    • Carry on, Jeeves: https://www.amazon.com/Carry-Jeeves-Dover-Thrift-Editions/dp/0486848957

    • Very Good, Jeeves: https://www.amazon.com/Very-Good-Jeeves-Wooster-Book-ebook/dp/B0051GST06

    • Right Ho, Jeeves: https://www.amazon.com/Right-Ho-Jeeves-P-Wodehouse-ebook/dp/B083FFDNHN/

    • Life: https://www.amazon.com/Life-Keith-Richards-ebook/dp/B003UBTX72/

    • My Name Is Barbra: https://www.amazon.com/My-Name-Barbra-Streisand/dp/0525429522

    • Clarkson’s Farm on Prime: https://www.amazon.com/Clarksons-Farm-Season-1/dp/B095RHJ52R

    • Schitt’s Creek on Hulu: https://www.hulu.com/series/schitts-creek-a2e7a946-9652-48a8-884b-3ea7ea4de273

    • Yellowstone on Peacock: https://www.peacocktv.com/stream-tv/yellowstone

    • Sam Altman on X: https://x.com/sama

    • Justin Kan on LinkedIn: https://www.linkedin.com/in/justinkan/

    • Alexis Ohanian on X: https://x.com/alexisohanian

    • Steve Huffman on LinkedIn: https://www.linkedin.com/in/shuffman56/

    • Breaking News: Condé Nast/Wired Acquires Reddit: https://techcrunch.com/2006/10/31/breaking-news-conde-nastwired-acquires-reddit/

    • Charles River Venture: https://www.crv.com/

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
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  • Ami Vora is the Chief Product Officer of Faire, which connects independent retailers and brands around the world. Before Faire, Ami spent over 15 years at Meta, including as VP of Product and Design for WhatsApp (2B+ users), VP of Product for Facebook’s ads system (now $130B of annual revenue), and director at Instagram. She began her career working on developer tools at Microsoft. In our conversation, we discuss:

    • Why execution eats strategy for breakfast

    • Using metaphor to rally teams around one shared goal

    • How to build cross-functional relationships

    • “Dinosaur brain,” “Toddler soccer,” and the “hill climbing” metaphors

    • A tactic for handling disagreement

    • Tips for working well with product-minded founders as a product leader

    • The story of Ami’s incredible 15-year journey from temp to VP at Meta

    • Much more

    —

    Brought to you by:

    • Sidebar—Accelerate your career by surrounding yourself with extraordinary peers.

    • Anvil—The fastest way to build software for documents.

    • User Testing—Human understanding. Human experiences.

    —

    Find the transcript at: https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora

    —

    Where to find Ami Vora:

    • LinkedIn: https://www.linkedin.com/in/amvora/

    • Substack: https://amivora.substack.com/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Ami’s background

    (02:00) The myth of perfection in success

    (07:55) Emotionally connecting with the job

    (09:55) Embracing curiosity in moments of challenge

    (13:16) Thinking in feedback loops

    (17:17) The “dinosaur brain” metaphor in product reviews

    (20:20) Strategies for conducting effective product reviews

    (26:33) Using metaphors and imagery to communicate your vision

    (29:35) The power of having a shared narrative

    (31:55) WhatsApp: an example of metaphor in action

    (34:44) Emulating people that inspire you

    (36:19) WhatsApp video calling

    (37:35) Why execution is greater than strategy

    (41:36) Time allotment for strategy vs. execution

    (45:10) How to become a better strategic thinker

    (47:59) The intricacies of implementing feedback

    (51:53) Being a female leader in tech

    (55:13) Advice for young women in tech

    (56:07) Setting goals and aligning incentives

    (01:01:40) Acknowledging hard truths

    (01:05:46) Lessons from transitioning to Faire

    (01:08:40) The importance of a good CPO/CEO relationship

    (01:11:17) Vetting heads of product and maintaining customer focus

    (01:12:40) How Ami went from intern to leading major products at Meta

    (01:14:53) The one thing you should do to be successful in product

    (01:17:25) Lightning round

    —

    Referenced:

    • Faire: https://www.faire.com/

    • Making Meta | Andrew “Boz” Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

    • Community Wisdom: AMA with Dan Hockenmaier + Facilitating a roadmap session, structuring product teams, navigating an acquisition, companies not needing PMs anymore, and much more: https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

    • Developing a growth model + marketplace growth strategy | Dan Hockenmaier (Faire, Thumbtack, Reforge): https://www.lennysnewsletter.com/p/developing-a-growth-model-marketplace

    • Dan Hockenmaier’s website: https://www.danhock.com/

    • On Reviews: https://boz.com/articles/reviews

    • Finding a global optimum always feels like a hill climb: https://www.linkedin.com/posts/amvora_finding-a-global-optimum-always-feels-like-activity-7074776143882588161-jhyy/

    • Dolores Park: https://sfrecpark.org/892/Mission-Dolores-Park

    • Rob Goldman on LinkedIn: https://www.linkedin.com/in/robgoldman/

    • Execution eats strategy for breakfast, but execution without strategy leads to burnout: https://rationalpm.substack.com/p/execution-eats-strategy-for-breakfast

    • The goal of a “strategy” is to change our own team’s behavior: https://amivora.substack.com/p/the-goal-of-a-strategy-is-to-change

    • The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer

    • Path to Power course outline: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf

    • Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey

    • Max Rhodes on LinkedIn: https://www.linkedin.com/in/max-rhodes/

    • Coupa Coffee: https://www.coupacafe.com/

    • Brandee Barker on LinkedIn: https://www.linkedin.com/in/brandeedbarker/

    • Year of Yes: How to Dance It Out, Stand In the Sun and Be Your Own Person: https://www.amazon.com/Year-Yes-Dance-Stand-Person/dp/1476777128

    • How to tell better stories | Matthew Dicks (Storyworthy): https://www.lennyspodcast.com/how-to-tell-better-stories-matthew-dicks-storyworthy/

    • A life of yes: Matthew Dicks at TEDxSomerville: https://www.youtube.com/watch?v=F3TaQFcaMk4

    • The Office on Peacock: https://www.peacocktv.com/stream-tv/the-office

    • 30 Rock on Peacock: https://www.peacocktv.com/watch-online/tv/30-rock/6240863759978157112

    • Dall-E-2: https://openai.com/index/dall-e-2/

    • ChatGPT: https://chatgpt.com

    • Fellow kettles: https://fellowproducts.com/products/stagg-ekg-electric-pour-over-kettle

    • TikTok’s “Roman Empire” Meme, Explained: https://www.forbes.com/sites/danidiplacido/2023/09/21/tiktoks-roman-empire-meme-explained/

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Tanguy Crusson is the product lead for Jira Product Discovery at Atlassian. In his more than 10 years at the company, he has been instrumental in taking several new products from zero to one, including HipChat, Statuspage, and Jira Product Discovery. In this episode, we dive deep into the struggles of innovating and building new products inside a large company. Tanguy shares candid stories about what worked, what didn’t, and his many hard-won lessons learned about how to successfully build 0 to 1. We cover:

    • Why large companies with so many advantages still fail at creating new products

    • Lessons learned from building HipChat

    • How to avoid common pitfalls like competitive myopia and premature scaling

    • Lessons learned from the acquisition and integration of Statuspage

    • Insights from the success of Jira Product Discovery

    • Tactics for protecting your “ugly babies”

    • The power of “lighthouse users”

    • The importance of having a “why now”

    • Much more

    —

    Brought to you by:

    • Vanta—Automate compliance. Simplify security

    • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

    • Coda—The all-in-one collaborative workspace

    —

    Find the transcript at: https://www.lennysnewsletter.com/p/building-0-to-1-inside-atlassian-tanguy-crusson

    —

    Where to find Tanguy Crusson:

    • X: https://x.com/tanguycrusson

    • LinkedIn: https://www.linkedin.com/in/tanguy-crusson-99832a

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Tanguy’s background

    (02:30) Tanguy’s journey at Atlassian

    (07:03) The challenges of innovating in large companies

    (10:42) Atlassian's high bar for excellence

    (12:58) The HipChat story: successes, failures, and lessons learned

    (20:47) Lessons learned from building HipChat

    (33:49) Statuspage: a journey of perseverance

    (39:48) Acquisition challenges and lessons

    (47:22) Strategic decisions: build, buy, or partner?

    (48:17) Learning to articulate "why now"

    (54:08) A quick summary of lessons in this episode

    (55:40) The success and pain of launching Jira Product Discovery

    (58:10) Incubating new products: the Point A program

    (01:00:13) Failure is the most likely outcome

    (01:04:15) Atlassian's four-phase approach to launching new products

    (01:09:20) Breaking rules without breaking trust

    (01:16:16) Early success and team autonomy

    (01:17:22) Innovating without disrupting existing customers

    (01:23:17) The Lighthouse Users program

    (01:30:00) Protecting and nurturing new ideas

    (01:36:14) Balancing innovation with personal well-being

    (01:38:17) A reminder to look after yourself

    (01:42:06) Lightning round

    —

    Referenced:

    • Atlassian: https://www.atlassian.com/

    • HipChat: https://community.atlassian.com/t5/Hipchat/ct-p/hipchat

    • Stride: https://community.atlassian.com/t5/Stride/ct-p/stride

    • Statuspage: https://www.atlassian.com/software/statuspage

    • Opsgenie: https://www.atlassian.com/software/opsgenie

    • Jira Product Discovery: https://www.atlassian.com/software/jira/product-discovery

    • HipChat billboard: https://x.com/HubSpot/status/654696998126272512

    • Announcing our new partnership with Slack: https://www.atlassian.com/blog/announcements/new-atlassian-slack-partnership

    • Slack shows it’s worried about Microsoft Teams with a full-page newspaper ad: https://www.theverge.com/2016/11/2/13497766/slack-microsoft-teams-new-york-times-ad

    • What Is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html

    • Jira: https://www.atlassian.com/software/jira

    • Confluence: https://www.atlassian.com/software/confluence

    • PagerDuty: https://www.pagerduty.com/

    • New Relic: https://newrelic.com/

    • BigPanda: https://www.bigpanda.io/

    • Transparent Uptime: http://www.transparentuptime.com/

    • Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

    • Figma: https://www.figma.com/

    • Lessons from Atlassian: Launching new products, getting buy-in, and staying ahead of the competition | Megan Cook (head of product, Jira): https://www.lennysnewsletter.com/p/lessons-from-atlassian-launching

    • Noah Weiss on LinkedIn: https://www.linkedin.com/in/noahw/

    • Tanguy’s LinkedIn post about “lighthouse users”: https://www.linkedin.com/posts/tanguy-crusson-99832a_lighthouse-users-one-of-the-pm-techniques-activity-7176654510801502210-hWNi/

    • Pixar Chief: Protect Your ‘Ugly Babies’ (Your Unsightly Ideas): https://www.forbes.com/sites/andyboynton/2014/03/17/pixar-chief-protect-your-ugly-babies-your-unsightly-ideas/

    • Atlas: https://www.atlassian.com/software/atlas

    • Point A: https://www.atlassian.com/point-a

    • Scott Farquhar on LinkedIn: https://www.linkedin.com/in/scottfarquhar

    • Who: A Method for Hiring: https://www.amazon.com/Who-Method-Hiring-HC-2008/dp/B004C79SRS/

    • Hakim’s Odyssey: Book 1: From Syria to Turkey: https://www.amazon.com/Hakims-Odyssey-Book-Syria-Turkey/dp/1637790007

    • Living with the Earth, Volume 1: Permaculture, Ecoculture: Inspired by Nature: https://www.amazon.com/Living-Earth-Gardeners-Permaculture-Ecoculture/dp/1856232603/

    • INRIA: https://en.wikipedia.org/wiki/French_Institute_for_Research_in_Computer_Science_and_Automation

    • How a Hydrofoil Works: https://web.mit.edu/2.972/www/reports/hydrofoil/hydrofoil.html

    • What Is Kitefoil or Foilboarding?: https://www.whenitswindy.com/wp/?page_id=534

    • Freediving: https://en.wikipedia.org/wiki/Freediving

    • Tanguy’s freediving stats: https://www.aidainternational.org/Athletes/Profile-00000000-0000-0000-0000-000000000a45

    • Perplexity: https://www.perplexity.com/

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Jeffrey Pfeffer teaches the single most popular (and somewhat controversial) class at Stanford’s Graduate School of Business: The Paths to Power. He’s also the author of 16 books, including 7 Rules of Power: Surprising—But True—Advice on How to Get Things Done and Advance Your Career. He has taught at Harvard, the London Business School, and IESE and has written for publications like Fortune and the Washington Post. Recognized by the Academy of Management and listed in the Thinkers50 Hall of Fame, Jeffrey also serves on several corporate and nonprofit boards, bringing his expertise to global audiences through seminars and executive education. In our conversation, we discuss:

    • Jeffrey’s seven rules of power

    • How individuals can acquire and use power in business

    • Networking, and how to do it effectively

    • How to build a non-cringe personal brand

    • How to increase your influence to amplify your impact

    • Examples and stories of people building power

    • Tradeoffs and challenges that come with power

    —

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer

    —

    Where to find Jeffrey Pfeffer:

    • X: https://x.com/JeffreyPfeffer

    • LinkedIn: https://www.linkedin.com/in/jeffrey-pfeffer-57a01b6/

    • Website: https://jeffreypfeffer.com/

    • Podcast: https://jeffreypfeffer.com/pfeffer-on-power/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Jeffrey’s background

    (02:54) Understanding discomfort with power

    (04:56) Power skills for underrepresented groups

    (07:51) The popularity and challenges of Jeffrey’s class at Stanford

    (12:21) The seven rules of power

    (13:03) Success stories from his course

    (15:43) Building a personal brand

    (21:11) Getting out of your own way

    (26:04) Breaking the rules to gain power

    (30:34) Networking relentlessly

    (40:10) Why Jeffrey says to “pursue weak ties”

    (42:00) Using your power to build more power

    (44:34) The importance of appearance and body language

    (47:15) Mastering the art of presentation

    (55:12) Examples of homework assignments that Jeffrey gives students

    (59:11) People will forget how you acquired power

    (01:03:58) More good people need to have power

    (01:10:49) The price of power and autonomy

    (01:17:13) A homework assignment for you

    —

    Referenced:

    • Gerald Ferris on LinkedIn: https://www.linkedin.com/in/gerald-r-ferris-5816b1b5/

    • Political Skill at Work: https://tarjomefa.com/wp-content/uploads/2015/10/4173-engilish.pdf

    • Laura Esserman, MD: https://cancer.ucsf.edu/people/esserman.laura

    • Taylor Swift’s website: https://www.taylorswift.com/

    • Matthew 7: https://www.biblegateway.com/passage/?search=Matthew%207&version=NIV

    • Mother Teresa quote: https://www.goodreads.com/quotes/2887-if-you-judge-people-you-have-no-time-to-love

    • Paths to Power course description: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf

    • 7 Rules of Power: https://jeffreypfeffer.com/books/7-rules-of-power/

    • The Knowing-Doing Gap: https://jeffreypfeffer.com/books/the-knowing-doing-gap/

    • Derek Kan on LinkedIn: https://www.linkedin.com/in/derekkan/

    • Mitt Romney on X: https://x.com/mittromney

    • Elaine Chao’s website: https://www.elainechao.com/

    • Tony Hsieh: https://en.wikipedia.org/wiki/Tony_Hsieh

    • Zappos: https://www.zappos.com/

    • How I Did It: Zappos’s CEO on Going to Extremes for Customers: https://hbr.org/2010/07/how-i-did-it-zapposs-ceo-on-going-to-extremes-for-customers

    • McKinsey & Company: https://www.mckinsey.com/

    • Bain & Company: https://www.bain.com/

    • BCG: https://www.bcg.com/

    • Keith Ferrazzi’s website: https://www.keithferrazzi.com/

    • Deloitte: https://www2.deloitte.com/

    • Tristan Walker: https://www.linkedin.com/in/tristanwalker/

    • Foursquare: https://foursquare.com/

    • Laura Chau on LinkedIn: https://www.linkedin.com/in/laura-chau/

    • Canaan Partners: https://www.canaan.com/

    • Andreessen Horowitz: https://a16z.com/

    • Sequoia Capital: https://www.sequoiacap.com/

    • Greylock: https://greylock.com/

    • The Women Who Venture (WoVen) Podcast: https://www.canaan.com/woven/podcasts

    • Imposter syndrome: https://www.psychologytoday.com/us/basics/imposter-syndrome

    • Gary Loveman and Harrah’s Entertainment: https://www.gsb.stanford.edu/faculty-research/case-studies/gary-loveman-harrahs-entertainment

    • “If you need help, just ask”: Underestimating compliance with direct requests for help: https://www.gsb.stanford.edu/faculty-research/publications/if-you-need-help-just-ask-underestimating-compliance-direct-requests

    • Life story of Kathleen Frances Fowler: https://www.forevermissed.com/kathleenfowler/lifestory

    • Jason Calacanis on LinkedIn: https://www.linkedin.com/in/jasoncalacanis/

    • Jason Calacanis: A Case Study in Creating Resources: https://www.gsb.stanford.edu/faculty-research/case-studies/jason-calacanis-case-study-creating-resources

    • You’re Invited: The Art and Science of Connection, Trust, and Belonging: https://www.amazon.com/Youre-Invited-Science-Cultivating-Influence/dp/0063030977

    • View from the Top: https://www.gsb.stanford.edu/experience/learning/guest-speakers/view-top

    • Omid Kordestani on LinkedIn: https://www.linkedin.com/in/omid-kordestani-46515151/

    • Netscape: https://en.wikipedia.org/wiki/Netscape

    • Esther Wojcicki on LinkedIn: https://www.linkedin.com/in/estherwojcicki/

    • Leanne Williams: https://med.stanford.edu/profiles/leanne-williams

    • Precision Psychiatry: Using Neuroscience Insights to Inform Personally Tailored, Measurement-Based Care: https://www.amazon.com/Precision-Psychiatry-Neuroscience-Personally-Measurement-Based/dp/1615371583

    • Mark Granovetter on LinkedIn: https://www.linkedin.com/in/mark-granovetter-8161704/

    • The Strength of Weak Ties: https://snap.stanford.edu/class/cs224w-readings/granovetter73weakties.pdf

    • Getting a Job: https://www.amazon.com/Getting-Job-Study-Contacts-Careers/dp/0226305813

    • Acting with Power: https://www.amazon.com/Acting-Power-More-Powerful-Believe/dp/110190397X

    • Articles by Herminia Ibarra: https://herminiaibarra.com/articles/

    • Kingdom of the Planet of the Ape: https://www.imdb.com/title/tt11389872/

    • Jim Collins’s website: https://www.jimcollins.com/

    • Dana Carney on LinkedIn: https://www.linkedin.com/in/danarosecarney/

    • Baba Shiv: https://www.gsb.stanford.edu/faculty-research/faculty/baba-shiv

    • Tony Hayward: https://en.wikipedia.org/wiki/Tony_Hayward

    • Lloyd Blankfein: https://en.wikipedia.org/wiki/Lloyd_Blankfein

    • Regis McKenna: https://en.wikipedia.org/wiki/Regis_McKenna

    • Jack Valenti: https://en.wikipedia.org/wiki/Jack_Valenti

    • Salman Rushdie quote: https://www.pinterest.com/pin/434175220328596286/

    • How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

    • Carole Robin’s 15% rule: https://pen-name.notion.site/Carole-Robin-on-Lenny-s-Podcast-dc7159208e4242428f4b11ebc92285eb

    • Karlie Kloss on Instagram: https://www.instagram.com/karliekloss

    • Lindsey Graham’s website: https://www.lindseygraham.com/

    • Was Microsoft’s Empire Built on Stolen Code? We May Never Know: https://www.wired.com/2012/08/ms-dos-examined-for-thef/

    • Who’s who of Jeffrey Epstein’s powerful friends, associates and possible co-conspirators: https://www.cnn.com/2019/08/12/us/jeffrey-epstein-associates-possible-accomplices/index.html

    • Why Did Martha Stewart Go to Prison? A Look Back at Her 2004 Fraud Case: https://people.com/martha-stewart-fraud-case-prison-sentence-look-back-8550277

    • Dianne Feinstein: https://www.congress.gov/member/dianne-feinstein/F000062

    • Richard Blum: https://en.wikipedia.org/wiki/Richard_C._Blum

    • Athena Care Network: https://www.athenacarenetwork.org

    • James G. March: https://en.wikipedia.org/wiki/James_G._March

    • Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

    • Trump Organization fined $1.6 million for tax fraud: https://apnews.com/article/politics-legal-proceedings-new-york-city-donald-trump-manhattan-e2f1d01525dafb64be8738c8b4f32085

    • Rudy Giuliani: https://en.wikipedia.org/wiki/Rudy_Giuliani

    • Harvard president resigns amid claims of plagiarism and antisemitism backlash: https://www.theguardian.com/education/2024/jan/02/harvard-president-claudine-gay-resigns

    • Stanford president resigns after fallout from falsified data in his research: https://www.npr.org/2023/07/19/1188828810/stanford-university-president-resigns

    • Rudy Crew: https://en.wikipedia.org/wiki/Rudy_Crew

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Uri Levine is the co-founder of Waze, the world’s largest community-based traffic and navigation app, acquired by Google for over $1 billion. He’s also founded nine other companies, been on the board of 20 companies, and advised more than 50 companies. He’s most recently the author of Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs, hailed by Steve Wozniak as the “Bible for entrepreneurs.” Uri is dedicated to creating impactful startups that solve real-world problems and has seen everything from failure to moderate success to big success. In our conversation, we dig into:

    • Why falling in love with the problem is key to startup success

    • The phases of the startup journey and how to navigate them

    • Why firing is more important than hiring

    • How Waze iterated to achieve product-market fit

    • Tactics for telling a compelling story when fundraising

    • Much more

    —

    Brought to you by:

    • Vanta—Automate compliance. Simplify security

    • Mercury—The powerful and intuitive way for ambitious companies to bank

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    —

    Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-uri-levine

    —

    Where to find Uri Levine:

    • X: https://twitter.com/urilevine1

    • LinkedIn: https://www.linkedin.com/in/uri-levine

    • Website: https://urilevine.com/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Uri’s background

    (02:50) Falling in love with the problem

    (09:03) Signs this is a big enough problem

    (10:54) The importance of passion

    (12:06) A pivot example

    (14:01) Where to find startup ideas

    (21:57) Finding product-market fit at Waze

    (29:45) The different phases of a startup journey

    (36:47) What investors don’t want to hear

    (39:53) Fundraising tips

    (48:02) How to make your presentations stronger

    (50:32) A wild fundraising story

    (53:46) Firing and hiring

    (59:50) The 30-day test

    (01:04:12) Understanding users

    (01:12:10) Talking to the right users

    (01:15:36) Lightning round

    —

    Referenced:

    • Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637741987

    • Waze: https://www.waze.com/

    • Ben Horowitz on LinkedIn: https://www.linkedin.com/in/behorowitz/

    • Ben Horowitz quote: https://quotefancy.com/quote/1635284/Ben-Horowitz-As-a-startup-CEO-I-slept-like-a-baby-I-woke-up-every-2-hours-and-cried

    • Michael Jordan quote: https://www.forbes.com/quotes/11194/#:~:text=I've%20lost%20almost%20300,that%20is%20why%20I%20succeed.

    • Steph Curry: https://en.wikipedia.org/wiki/Stephen_Curry

    • How Airbnb Used Word of Mouth to Change the Travel Industry Forever: https://truested.com/story/airbnb

    • Space Mountain: https://en.wikipedia.org/wiki/Space_Mountain_(Disneyland)

    • How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence

    • Steve Wozniak on LinkedIn: https://www.linkedin.com/in/wozniaksteve/

    • Uri’s post about the conference in Guatemala with Steve Wozniak: https://www.linkedin.com/posts/uri-levine_jewishnewyear-speakers-book-activity-6980089544079486976-0ADa/

    • Leonardo da Vinci quote: https://www.goodreads.com/quotes/9010638-simplicity-is-the-ultimate-sophistication-when-once-you-have-tasted

    • Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead

    • Nana Korobi Ya Oki: https://ikigaitribe.com/vlog/nana-korobi-ya-oki/

    • That Will Never Work: The Birth of Netflix and the Amazing Life of an Idea: https://www.amazon.com/That-Will-Never-Work-Netflix/dp/0316530204

    • Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299

    • 8 Great Chess Apps for Beginners and Grand Masters: https://www.wired.com/story/best-chess-apps/

    • Pontera: https://pontera.com/

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Cameron Adams is the co-founder and chief product officer of Canva. Canva is one of the world’s most valuable private software companies, used by 95% of Fortune 500 companies. Since its launch in 2013, Canva has grown to over 150 million monthly users in more than 190 countries, generating $2.3 billion in annual revenue. Prior to Canva, Cameron ran a design consultancy, worked at Google on Google Wave, and founded the email startup Fluent. He is also an author of five web design books and a regular speaker at global conferences. In our conversation, we discuss:

    • Why they spent a year building their minimum viable product (MVP) before launch

    • Why Canva has no managers, and their unique approach to coaching and performance reviews

    • Why they encourage employees to “give away their Legos”

    • Insights into Canva’s SEO growth strategy

    • Their three-pillar framework for integrating AI into their product

    • Stories from the early days

    —

    Brought to you by:

    • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

    • Attio—The powerful, flexible CRM for fast-growing startups

    • Vanta—Automate compliance. Simplify security.

    —

    Find the transcript at: https://www.lennysnewsletter.com/p/inside-canva-with-cameron-adams

    —

    Where to find Cameron Adams:

    • X: https://twitter.com/themaninblue

    • LinkedIn: https://www.linkedin.com/in/themaninblue

    • Website: https://themaninblue.com/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Cameron’s background

    (02:00) Reflecting on the success of Canva

    (04:50) Reflecting on hard times

    (10:01) Canva’s product-obsessed culture

    (12:02) Why they prioritize internal promotions and hires

    (13:56) What makes Canva unique

    (16:31) The concept of giving away your Legos

    (21:44) Why Canva has no managers

    (24:29) Product management at Canva

    (27:56) Reflections on working with a married couple

    (30:37) Why they spent a year building their MVP before launch

    (33:49) Advice for building an MVP

    (41:23) Canva’s onboarding transformation

    (44:25) Canva’s SEO strategy

    (50:37) The success of Canva’s freemium strategy

    (54:24) Integrating AI into Canva’s product

    (01:01:50) Where to find Cameron

    —

    Referenced:

    • Canva: https://www.canva.com/

    • Melanie Perkins on LinkedIn: https://www.linkedin.com/in/melanieperkins

    • Cliff Obrecht on LinkedIn: https://www.linkedin.com/in/cliff-obrecht-79ba9920

    • Jennie Rogerson, Head of People, LinkedIn post about “season opener” events: https://www.linkedin.com/posts/jennierogerson_season-opener-is-one-of-my-favourite-events-activity-7006815614556135424-73bD/

    • Game of Thrones on HBO: https://www.hbo.com/game-of-thrones

    • Woodstock: https://en.wikipedia.org/wiki/Woodstock

    • ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups/

    • Minimum viable product (MVP): https://www.productboard.com/glossary/minimum-viable-product-mvp

    • Canva’s SEO Strategy Is Elite: https://thegrowthplaybook.substack.com/p/canvas-seo-strategy-is-elite

    • The SEO Strategy That Led Canva to a $40 Billion Valuation: https://www.youtube.com/watch?v=INyGKt6LAqM

    • Andrianes Pinantoan on LinkedIn: https://www.linkedin.com/in/andrianes/

    • Canva Create: https://www.canva.com/canva-create/

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Matt Dixon is one of the world’s foremost experts in sales and the author of The Challenger Sale, which sold over a million copies worldwide and was a #1 Amazon and Wall Street Journal bestseller. His most recent book, The JOLT Effect, focuses on overcoming customer indecision—one of the biggest challenges to closing deals. Outside of writing, Matt co-founded DCM Insights, a boutique consultancy helping organizations understand customer behavior, and is a frequent contributor to the Harvard Business Review, with more than 20 print and online articles to his credit. In our conversation, we discuss:

    • Why 40% to 60% of qualified sales opportunities are lost due to customer indecision

    • Why dialing up FOMO doesn’t work, and what to do instead

    • The “pings and echoes” technique to catch issues early

    • The JOLT method for overcoming indecision

    • Key lessons from The Challenger Sale

    • Practical examples of how to apply these principles to close more deals

    —

    Brought to you by:

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    • Heap—Cross-platform product analytics that converts, engages, and retains customers

    —

    Find the transcript at: https://www.lennysnewsletter.com/p/close-more-deals-matt-dixon

    —

    Where to find Matt Dixon:

    • LinkedIn: https://www.linkedin.com/in/matthewxdixon

    • Website: https://www.jolteffect.com/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Matt’s background

    (01:57) The research behind Matt’s books

    (06:08) Insights from The JOLT Effect

    (10:15) FOMO vs. FOMU

    (18:18) An example of selling software

    (26:04) The JOLT method Step 1: Judge their level of indecision

    (29:41) The “pings and echoes” technique

    (34:49) Step 2: Offer a recommendation

    (38:36) Step 3: Limit the exploration

    (41:43) Step 4: Take risk off the table

    (45:58) When to hit the pause button with a customer

    (47:27) Insights from The Challenger Sale

    (49:07) An example of a challenger sale

    (55:23) Where to find Matt

    —

    Referenced:

    • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting

    • The Challenger Sale: Taking Control of the Customer Conversation: https://www.amazon.com/Challenger-Sale-Control-Customer-Conversation/dp/0670922854

    • The JOLT Effect: How High Performers Overcome Customer Indecision: https://www.amazon.com/JOLT-Effect-Performers-Overcome-Indecision/dp/0593538102

    • Gartner acquires CEB: https://www.gartner.com/en/about/acquisitions/history/ceb-acquisition

    • Tiger King on Netflix: https://www.netflix.com/title/81115994

    • Why sourdough went viral: https://www.economist.com/1843/2020/08/04/why-sourdough-went-viral

    • Neil Rackham: https://en.wikipedia.org/wiki/Neil_Rackham

    • Status quo bias in decision-making: https://en.wikipedia.org/wiki/Status_quo_bias

    • Omission bias: https://thedecisionlab.com/biases/omission-bias

    • Gartner Magic Quadrant & Critical Capabilities: https://www.gartner.com/en/research/magic-quadrant

    • Dunning-Kruger effect: https://en.wikipedia.org/wiki/Dunning%E2%80%93Kruger_effect

    • Stop Losing Sales to Customer Indecision: https://hbr.org/2022/06/stop-losing-sales-to-customer-indecision

    • Dentsply Sirona: https://www.dentsplysirona.com/

    • “We happy?” Briefcase scene from Tarantino’s Pulp Fiction: https://www.youtube.com/watch?v=FGchDuOpbhE

    • Nupro Freedom Cordless Prophy System: https://www.dentsplysirona.com/en-us/discover/discover-by-category/preventive/hygiene-handpieces.html

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Bangaly Kaba was an early growth PM at Facebook, head of growth at Instagram, and VP of Product at Instacart and is currently Director of Product at YouTube overseeing a global team working on creator monetization. Bangaly has also been a growth advisor to dozens of companies, including Twitter, on the board of multiple companies, and is an active angel investor. In our conversation, we discuss:

    • A simple framework for choosing where to work and what to work on

    • The importance of “understand work”

    • The “adjacent users” theory and how it can help you drive growth

    • Advice for coaching product managers

    • Invaluable lessons from his time at Instagram, Facebook, and YouTube

    • Much more

    —

    Brought to you by:

    • Uizard—AI-powered prototyping for visionary product leaders

    • Mercury—The powerful and intuitive way for ambitious companies to bank

    • Vanta—Automate compliance. Simplify security.

    —

    Find the transcript and references at: https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba

    —

    Where to find Bangaly Kaba:

    • X: https://twitter.com/iambangaly

    • LinkedIn: https://www.linkedin.com/in/iambangaly/

    • Instagram: https://www.instagram.com/iambangaly/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Bangaly’s background

    (06:31) Choosing where to work and what to work on

    (08:39) The impact factor

    (10:53) Evaluating the environment

    (15:53) The manager component

    (18:27) The skills part of the equation

    (23:49) Advice on finding a mentor

    (25:42) The power of “understand work”

    (31:17) Operationalizing understand work

    (37:55) Balancing understand work

    (41:25) Managing complex change

    (45:26) Effective management of product managers

    (51:35) The role of product managers as coaches and team leaders

    (54:52) Driving growth through flywheels and value proposition

    (01:03:14) Understanding adjacent users

    (01:08:41) The role of partnerships and SEO in Instagram’s early growth

    (01:16:08) The secret behind Instagram’s growth

    (01:25:37) Lessons from Facebook

    (01:29:15) Failure corner

    (01:31:58) Lightning round

    —

    Referenced:

    • Impact = Environment x Skills: How to Make Career Decisions: https://www.reforge.com/blog/how-to-make-career-decisions

    • Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey

    • Casey Winters’s blog: https://caseyaccidental.com/

    • Ben Thompson’s newsletter: https://stratechery.com/about/

    • Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company

    • George Lee on LinkedIn: https://www.linkedin.com/in/geolee/

    • Bangaly Kaba: The Path to 1 Billion: Lessons Learned from Growing Instagram—CXL LIVE 2018: https://www.youtube.com/watch?v=L9ZHlb6kj_E

    • What Is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html

    • Bloom’s taxonomy: https://en.wikipedia.org/wiki/Bloom%27s_taxonomy

    • Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/

    • Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger/

    • LeBron James: https://en.wikipedia.org/wiki/LeBron_James

    • Kobe Bryant: https://en.wikipedia.org/wiki/Kobe_Bryant

    • Mike Krzyzewski: https://en.wikipedia.org/wiki/Mike_Krzyzewski

    • John Calipari: https://en.wikipedia.org/wiki/John_Calipari

    • Stripe: https://stripe.com/

    • Chief: https://chief.com/

    • Jobs to be done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90

    • The Adjacent User: https://brianbalfour.com/quick-takes/the-adjacent-user

    • How the biggest consumer apps got their first 1,000 users: https://www.lennysnewsletter.com/p/how-the-biggest-consumer-apps-got

    • Alex Zhu on LinkedIn: https://www.linkedin.com/in/keepsilence/

    • From Brush to Canvas with Alex Zhu of Musical.ly: https://www.youtube.com/watch?v=ey15v81pwII

    • Selena Gomez on Instagram: https://www.instagram.com/selenagomez/

    • Kim Kardashian on Instagram: https://www.instagram.com/kimkardashian/

    • Rob Andrews on LinkedIn: https://www.linkedin.com/in/robby-andrews-64669720/

    • Instagram’s growth speeds up as it hits 700 million users: https://techcrunch.com/2017/04/26/instagram-700-million-users/

    • Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484

    • Deep Work: Rules for Focused Success in a Distracted World: https://www.amazon.com/Deep-Work-Focused-Success-Distracted/dp/1455586692

    • Start at the End: How to Build Products That Create Change: https://www.amazon.com/Start-End-Products-Create-Change/dp/0525534423

    • Flighty app: https://www.flightyapp.com/

    • Adam Grant on Instagram: https://www.instagram.com/adamgrant/

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Kenneth Berger coaches startup leaders on how to prevent burnout, advocate for their desired lifestyle, and make a meaningful impact on the world. He’s spent more than 20 years in the tech industry, is a former founder backed by top investors, and was the first product manager at Slack. Kenneth’s core mission is to help startup leaders change the world by learning to ask for what they want, living with integrity, and building genuine relationships even with the people they find most challenging. Currently he is writing a book, Ask for What You Want, in which he aims to share his actionable strategies for creating change in the world. In our conversation, we explore:

    • Why asking for what you want is so impactful

    • Three steps to effectively ask for what you want

    • Challenges that arise when people struggle to ask for what they want

    • Why hearing “no” is a normal part of the process

    • The “dream behind the complaint” technique for uncovering desires

    • Kenneth’s experience of being fired three times from Slack

    • How embracing fear and discomfort is key to getting what you want

    • Why discipline is overrated

    —

    Brought to you by:

    • Sidebar—Accelerate your career by surrounding yourself with extraordinary peers

    • Webflow—The web experience platform

    • Vanta—Automate compliance. Simplify security

    —

    Find the transcript at: https://www.lennysnewsletter.com/p/ask-for-what-you-want-kenneth-berger

    —

    Where to find Kenneth Berger:

    • X: https://twitter.com/kberger

    • Threads: https://www.threads.net/@kberger

    • LinkedIn: https://www.linkedin.com/in/kberger/

    • Website: https://kberger.com/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Kenneth’s background

    (04:31) The importance of asking for what you want

    (06:36) Challenges that arise when people struggle to ask for what they want

    (08:09) A personal example of failing to ask for what you want

    (09:17) Signs this is a skill you need to work on

    (10:49) How to get better at knowing what you want

    (15:28) Why hearing “no” is a normal part of the process

    (17:29) Getting a “yes” vs. a “hell yes”

    (19:20) Step 1: Articulate what you want

    (24:07) Doing an integrity check

    (26:56) Step 2: Ask for what you want intentionally

    (30:45) Understanding your influence

    (34:48) Using complaints as inspiration

    (36:24) Internal family systems

    (38:00) Giving feedback

    (41:24) Step 3: Accept the response

    (45:22) Kenneth’s experience of being fired three times from Slack

    (57:30) Advice on being the first PM at a company or startup

    (01:04:58) Contrarian corner: anti-discipline

    (01:05:52) Lightning round

    —

    Referenced:

    • Joining as the first product manager: https://www.lennysnewsletter.com/p/joining-as-the-first-product-manager

    • Internal Family Systems: https://ifs-institute.com/

    • How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

    • Leaders in Tech: https://leadersintech.org/

    • The Three Realities Framework | The 15% Rule | Feedback Guidelines: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

    • T-group weekends at Stanford: https://www.gsb.stanford.edu/experience/learning/leadership/interpersonal-dynamics/facilitation-training-program/intro-tgroup

    • DBT skill DEAR MAN: https://www.therapistaid.com/therapy-worksheet/dbt-dear-man

    • Dialectical behavior therapy (DBT): https://my.clevelandclinic.org/health/treatments/22838-dialectical-behavior-therapy-dbt

    • Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

    • Stewart Butterfield on LinkedIn: https://www.linkedin.com/in/butterfield/

    • How to fire people with grace, work through fear, and nurture innovation | Matt Mochary (CEO coach): https://www.lennysnewsletter.com/p/how-to-fire-people-with-grace-work

    • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

    • Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice

    • Jonny Miller’s Nervous System Mastery course: https://nsmastery.com/lenny

    • Managing nerves, anxiety, and burnout | Jonny Miller (Nervous System Mastery): https://www.lennysnewsletter.com/p/managing-nerves-anxiety-and-burnout

    • The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE

    • Break Point on Netflix: https://www.netflix.com/title/81569920

    • Living on Netflix: https://www.netflix.com/title/81582076

    • Wimbledon tennis: https://www.wimbledon.com

    • Wenshan Baozhong tea: https://redblossomtea.com/products/wenshan-baozhong?variant=31629962820

    • Tea From Taiwan: https://www.teafromtaiwan.com/

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Jag Duggal is chief product officer at Nubank, a decacorn neobank founded in Brazil. It’s valued at over $30 billion, is bigger than Coinbase, Robinhood, Affirm, and SoFi combined, has 100 million customers (more than Bank of America!) while only operating in three countries in Latin America, and 80% to 90% of its growth comes through word of mouth. Prior to Nubank, Jag was a director of product management at Facebook, a senior vice president at Quantcast, and a product leader at Google. In our conversation, we discuss:

    • How Nubank builds a fanatical user base

    • Tactics for driving word-of-mouth growth

    • Measuring customer love through the Sean Ellis score

    • The importance of strategic clarity

    • The role of category design in creating successful products

    • Why companies should strive to be “fundamentally different,” not “incrementally better”

    • Nubank’s vision for an AI-powered banking future

    —

    Brought to you by:

    • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

    • Mercury—The powerful and intuitive way for ambitious companies to bank

    • OneSchema—Import CSV data 10x faster

    —

    Find the transcript at: https://www.lennysnewsletter.com/p/be-fundamentally-different-jag-duggal

    —

    Where to find Jag Duggal:

    • LinkedIn: https://www.linkedin.com/in/jagduggal/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Jag’s background

    (04:34) Nubank’s remarkable achievements

    (06:01) Nubank’s product development process

    (11:23) Nubank’s values

    (12:16) Building products people love fanatically

    (15:21) The Sean Ellis score

    (21:27) An example project using the Sean Ellis score

    (25:07) Picking up the phone and calling customers

    (28:20) The importance of starting small and iterating

    (30:42) Pushing back effectively

    (34:10) Uncovering pain points through customer research

    (37:53) An example of setting a clear hypothesis

    (42:01) Developing a strategy

    (52:16) “Be fundamentally different, not incrementally better”

    (53:10) Category design

    (57:37) Nubank’s founding story and goals for the future

    (01:00:46) Advice for adding new product lines

    (01:03:46) The future of fintech and banking

    (01:09:23) AI corner

    (01:12:34) Failure corner

    (01:20:24) Key takeaways

    (01:22:11) Lightning round

    —

    Referenced:

    • Nubank: https://nubank.com.br/en/

    • Coinbase: https://www.coinbase.com/

    • Robinhood: https://www.robinhood.com/

    • SoFi: https://www.sofi.com/

    • Affirm: https://www.affirm.com/

    • Lemonade: https://www.lemfi.com/

    • Bank of America: https://www.bankofamerica.com/

    • Nubank achieves a world record with more than 7 million people participating in NuBolão in one month: https://building.nubank.com.br/nubank-achieves-world-record-with-nubolao

    • Nu México carries out first financial transaction 20 meters under the depth of the sea: https://www.bnamericas.com/en/news/nu-mexico-carries-out-first-financial-transaction-20-meters-under-the-depth-of-the-sea

    • David Vélez on LinkedIn: https://www.linkedin.com/in/david-v%C3%A9lez-1004875

    • Cristina Junqueira on LinkedIn: https://www.linkedin.com/in/crisjunqueira

    • Edward Wible on LinkedIn: https://www.linkedin.com/in/adamedwardwible

    • Sequoia Capital: https://www.sequoiacap.com/

    • Churrascaria: https://en.wikipedia.org/wiki/Churrascaria

    • Nubank’s real foundation: our culture and values: https://building.nubank.com.br/nubank-culture-and-values/

    • Working Backwards Press Release Template and Example: https://www.linkedin.com/pulse/working-backwards-press-release-template-example-ian-mcallister/

    • Sean Ellis test: https://productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c

    • How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket

    • Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

    • Ultravioleta: Nubank expands its premium card offer and adds new features on the product’s first anniversary: https://international.nubank.com.br/company/ultravioleta-nubank-expands-its-premium-card-offer-and-adds-new-features-on-the-products-first-anniversary/

    • Jeff Bezos: Amazon and Blue Origin | Lex Fridman Podcast #405: https://www.youtube.com/watch?v=DcWqzZ3I2cY

    • The Innovation Method Behind Swiffer Madness: https://www.fastcompany.com/3006797/innovation-method-behind-swiffer-madness

    • Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/

    • Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard

    • Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239

    • The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240/

    • How to become a category pirate | Christopher Lochhead (author of Play Bigger, Niche Down, Category Pirates, more): https://www.lennysnewsletter.com/p/how-to-become-a-category-pirate-christopher

    • Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets: https://www.amazon.com/Play-Bigger-Dreamers-Innovators-Dominate/dp/0062407619

    • Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X

    • A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

    • Citi: https://www.citi.com/

    • Santander Bank: https://www.santanderbank.com/

    • Fidji Sumo on LinkedIn: https://www.linkedin.com/in/fidjisimo/

    • Harvard Kennedy School: https://www.hks.harvard.edu/

    • Susan Wojcicki on LinkedIn: https://www.linkedin.com/in/susan-wojcicki-b136a99/

    • Coldplay—“Lost+” ft. Jay-Z: https://www.youtube.com/watch?v=PkCDRm_YRFg

    • Google Buys DoubleClick for $3.1 Billion: https://www.nytimes.com/2007/04/14/technology/14DoubleClick.html

    • Real-time bidding: https://support.google.com/authorizedbuyers/answer/6136272

    • From Third World to First: The Singapore Story: 1965-2000: https://www.amazon.com/Third-World-First-Singapore-1965-2000/dp/0060197765/

    • The Gilded Age on HBO: https://www.hbo.com/the-gilded-age

    • Lomi: https://lomi.com/

    • Nubank careers: https://international.nubank.com.br/careers/

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Vikrama Dhiman heads all things product at Gojek, including product management, design, program management, and research, across Indonesia, Singapore and India. He has over 16 years of experience building internet products, consults with Fortune 500 companies, and is among the most well-known and respected product leaders in all of Asia. In our conversation, we discuss:

    • The most common traits among successful product managers

    • The 3 W’s framework for PM career growth

    • The Four A’s of leveling up in product management

    • The right way to push back as a PM

    • Common pitfalls that stall PM careers

    • Vikrama’s advice for transitioning into product management

    • Why intent alone is not enough

    —

    Brought to you by:

    • Uizard—AI-powered prototyping for visionary product leaders

    • Webflow—The web experience platform

    • Coda—The all-in-one collaborative workspace

    —

    Find the transcript at: https://www.lennysnewsletter.com/p/a-framework-for-pm-skill-development

    —

    Where to find Vikrama Dhiman:

    • X: https://twitter.com/vikramadhiman

    • LinkedIn: https://www.linkedin.com/in/vikrama/

    • Website: https://www.vikramadhiman.com/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Vikrama’s background

    (03:56) Three common traits among great PMs

    (07:09) The first W: What you produce

    (15:40) The second W: What you bring to the table

    (18:58) The third W: What’s your operating model?

    (20:36) Three traits that make you a great PM to work with

    (21:49) How to improve the quality and quantity of your outputs

    (23:26) The art of the pushback

    (26:55) Common factors that impede career growth

    (33:39) Vikrama’s personal reflections

    (39:33) Choosing which skill(s) to focus on developing

    (46:28) The ambiguity of the PM role

    (51:47) The 8 axis for PM growth

    (56:57) Contrarian corner: Why intent alone is not enough

    (59:30) Lightning round

    —

    Referenced:

    • Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek): https://www.lennysnewsletter.com/p/taxi-mafias-cash-vaults-and-100-mom

    • How to scrappily hire for, measure, and unlock growth | Crystal Widjaja, Gojek and Kumu: https://www.lennysnewsletter.com/p/how-to-hire-for-measure-and-unlock

    • Gojek: https://www.gojek.com/en-id

    • SQL: https://en.wikipedia.org/wiki/SQL

    • Oracle: https://www.oracle.com/

    • Crystal Widjaja on LinkedIn: https://www.linkedin.com/in/crystalwidjaja

    • Raditya Wibowo: https://www.linkedin.com/in/raditya-wibowo-a0845436/?originalSubdomain=id

    • Sidu Ponnappa on LinkedIn: https://www.linkedin.com/in/sidup

    • Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack): https://www.lennysnewsletter.com/p/leveraging-mentors-to-uplevel-your

    • Kevin Aluwi on LinkedIn: https://www.linkedin.com/in/kaluwi/

    • Workday: https://www.workday.com/

    • Salesforce: https://www.salesforce.com/

    • Small Data: The Tiny Clues That Uncover Huge Trends: https://www.amazon.com/Small-Data-Clues-Uncover-Trends/dp/1250080681

    • Originals: How Non-Conformists Move the World: https://www.amazon.com/Originals-How-Non-Conformists-Move-World/dp/014312885X

    • Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555

    • Miss Congeniality on Prime Video: https://www.amazon.com/Miss-Congeniality-Sandra-Bullock/dp/B002R5HQDK

    • Schitt’s Creek on Prime Video: https://www.amazon.com/Schitts-Creek/dp/B083LDRW9F

    • DramaBox: https://www.dramaboxapp.com/

    • Am I Overthinking This?: Over-Answering Life’s Questions in 101 Charts: https://www.amazon.com/Am-Overthinking-This-Over-answering-questions/dp/1452175861/

    • Crazy Rich Asians on Prime Video: https://www.amazon.com/Crazy-Rich-Asians-Constance-Wu/dp/B07JGJFXBF

    • 9 Best Hawker Centers in Singapore—and What to Eat There: https://www.afar.com/magazine/best-hawker-centers-in-singapore-and-what-to-eat-there

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Hamilton Helmer is one of the world’s leading experts on business strategy and the author of the seminal book 7 Powers: The Foundations of Business Strategy, which provides a comprehensive framework for understanding what it really takes to achieve and sustain a competitive advantage. With more than three decades of experience in the strategic consulting industry, Hamilton has advised over 200 companies—from burgeoning startups to Fortune 100 giants—on how to identify, build, and leverage their unique strategic powers. In our conversation, we discuss:

    • Potential sources of power that startups should develop from an early stage

    • Common misconceptions among companies about the types of power they possess

    • How power relates to strategy

    • The difference between a moat and a power

    • Practical strategies for non-leaders to leverage insights about power and strategy in their work

    • AI’s impact on competitive advantages and barriers to entry

    —

    Brought to you by:

    • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

    • Vanta—Automate compliance. Simplify security

    • Paragon—Ship every SaaS integration your customers want

    —

    Find the transcript and references at: https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

    —

    Where to find Hamilton Helmer:

    • X: https://twitter.com/hamiltonhelmer

    • LinkedIn: https://www.linkedin.com/in/hamilton-helmer-42983/

    • Website: https://7powers.com/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Hamilton’s background

    (04:08) When power becomes important

    (08:24) How strategy relates to power

    (12:09) How power informs strategy

    (14:46) The sequence of powers

    (21:13) Common misconceptions

    (24:39) Network effects vs. network economies

    (26:58) Uber’s success

    (29:16) Moats vs. powers

    (31:12) Strategies for non-leaders to leverage power and strategy

    (37:51) Advice on how to become a strategic thinker

    (39:27) AI’s impact on the seven powers

    (45:43) Why moving fast is not a power

    (50:24) Three things that create value in a company

    (51:16) The debt trajectory of the U.S.

    (56:35) Optimism for the future

    (59:25) Lightning round

    —

    Referenced:

    • 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

    • John von Neumann: https://en.wikipedia.org/wiki/John_von_Neumann

    • Pearl Harbor: https://www.history.com/topics/world-war-ii/pearl-harbor

    • Where the Japanese Went Wrong at Pearl Harbor: https://pearlharbor.org/blog/where-japanese-went-wrong-pearl-harbor/

    • The ‘7 Powers’ of business success—from one of Netflix’s early investors: https://www.qualitycompounders.com.au/post/the-7-powers-of-business-success-from-one-of-netflix-s-early-investors

    • 7 Powers: Foundations of Business Strategy (Key Takeaways): https://www.linkedin.com/pulse/7-powers-foundations-business-strategy-key-takeaways-nikita-maloo/

    • Strategy Capital: https://strategycapital.com/

    • Warren Buffett: https://www.forbes.com/profile/warren-buffett/

    • Charlie Munger: https://www.forbes.com/profile/charles-munger/

    • Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.stripe.press/poor-charlies-almanack

    • Bill Gates reveals why Warren Buffett was an invaluable source of support during the stormiest period of his career: https://www.businessinsider.com/bill-gates-interview-warren-buffett-support-microsoft-antitrust-lawsuit-2019-6

    • Billionaire Warren Buffett’s Secret Love Affair With Castles, Revealed: https://www.thestreet.com/opinion/billionaire-warren-buffett-s-secret-love-affair-with-castles-revealed-14290973

    • Netflix didn’t kill Blockbuster—how Netflix almost lost the movie rental wars: https://www.cnbc.com/2020/09/22/how-netflix-almost-lost-the-movie-rental-wars-to-blockbuster.html

    • Michael Porter on LinkedIn: https://www.linkedin.com/in/professorporter/

    • What Is Strategy?: https://hbr.org/1996/11/what-is-strategy

    • TSMC: https://www.tsmc.com/english

    • Toyota Production System: https://en.wikipedia.org/wiki/Toyota_Production_System

    • America will be left with ‘severe, irreversible scars’ if national debt goes unchecked. Now, a blockbuster report warns the bill is higher than believed, hitting $141T by 2054: https://fortune.com/2024/04/01/america-social-economic-scars-us-debt-gomes-price/

    • Ben S. Bernanke: https://www.federalreservehistory.org/people/ben-s-bernanke

    • Forty-four of 50 U.S. states worsen inequality with ‘upside-down’ taxes: https://www.theguardian.com/us-news/2024/jan/10/states-wealth-inequality-taxes

    • Joseph A. Schumpeter: https://en.wikipedia.org/wiki/Joseph_Schumpeter

    • Theory of Economic Development: https://www.amazon.com/Theory-Economic-Development-Science-Classics/dp/0878556982

    • The Road to Reality: A Complete Guide to the Laws of the Universe: https://www.amazon.com/Road-Reality-Complete-Guide-Universe/dp/0679776311

    • The Gene: An Intimate History: https://www.amazon.com/Gene-Intimate-History-Siddhartha-Mukherjee/dp/147673352X

    • American Fiction on Prime Video: https://www.amazon.com/American-Fiction-Jeffrey-Wright/dp/B0CQKR72NX

    • Farahan Sarouk rugs: https://nazmiyalantiquerugs.com/persian-sarouk-farahan-rugs/

    • Rory Sutherland on LinkedIn: https://www.linkedin.com/in/rorysutherland

    • Ogilvy: https://www.ogilvy.com/

    • Clint Eastwood quote: https://www.brainyquote.com/quotes/clint_eastwood_168005

    • Winston Churchill: https://en.wikipedia.org/wiki/Winston_Churchill

    • Michelangelo, God’s Architect: The Story of His Final Years and Greatest Masterpiece: https://www.amazon.com/Michelangelo-Gods-Architect-Greatest-Masterpiece/dp/0691195498

    • The Last Judgment: https://en.wikipedia.org/wiki/The_Last_Judgment_(Michelangelo)

    • Theodore Roosevelt: https://www.whitehouse.gov/about-the-white-house/presidents/theodore-roosevelt/

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Annie Duke is a former professional poker player, a decision-making expert, and a special partner at First Round Capital. She is the author of Thinking in Bets (a national bestseller) and Quit: The Power of Knowing When to Walk Away and the co-founder of the Alliance for Decision Education, a nonprofit whose mission is to improve lives by empowering students through decision skills education. In our conversation, we cover:

    • What Annie learned from the late Daniel Kahneman

    • The power of pre-mortems and “kill criteria”

    • The relationship between money and happiness

    • The power of “mental time travel”

    • The nominal group technique for better decision quality

    • How First Round Capital improved their decision-making process

    • Many tactical decision-making frameworks

    —

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke

    —

    Where to find Annie Duke:

    • X: https://twitter.com/AnnieDuke

    • LinkedIn: https://www.linkedin.com/in/annie-duke/

    • Website: https://www.annieduke.com/

    • Substack: https://www.annieduke.com/substack/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Annie’s background

    (03:53) Lessons from Daniel Kahneman: humility, curiosity, and open-mindedness

    (09:15) The importance of unconditional love in parenting

    (15:15) Mental time travel and “nevertheless”

    (20:06) The extent of improvement possible in decision-making

    (24:54) Independent brainstorming for better decisions

    (35:36) Making sure people feel heard

    (42:41) The “3Ds” framework to make better decisions

    (44:49) Decision quality

    (55:46) Improving decision-making at First Round Capital

    (01:05:05) Using pre-mortems and kill criteria

    (01:10:15) Making explicit what’s implicit

    (01:10:55) The challenges of quitting and knowing when to walk away

    (01:19:23) Where to find Annie

    —

    Referenced:

    • Daniel Kahneman, Who Plumbed the Psychology of Economics, Dies at 90: https://www.nytimes.com/2024/03/27/business/daniel-kahneman-dead.html

    • Adversarial collaboration: https://en.wikipedia.org/wiki/Adversarial_collaboration

    • Does more money correlate with greater happiness?: https://penntoday.upenn.edu/news/does-more-money-correlate-greater-happiness-Penn-Princeton-research#

    • Income and emotional well-being: A conflict resolved: https://pubmed.ncbi.nlm.nih.gov/36857342/

    • Strategic decisions: When can you trust your gut?: https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/strategic-decisions-when-can-you-trust-your-gut

    • Cass Sunstein on X: https://twitter.com/CassSunstein

    • Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside

    • A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

    • First Round Capital: https://firstround.com/

    • Brett Berson on X: https://twitter.com/brettberson

    • Renegade Partners: https://www.renegadepartners.com/

    • Renata Quintini on X: https://twitter.com/rquintini

    • Roseanne Wincek on X: https://twitter.com/imthemusic

    • Josh Kopelman on X: https://twitter.com/joshk

    • Bill Trenchard on X: https://twitter.com/btrenchard

    • Linnea Gandhi on X: https://twitter.com/linneagandhi

    • Maurice Schweitzer on X: https://twitter.com/me_schweitzer

    • Problems with premortems: https://sjdm.org/presentations/2021-Poster-Gandhi-Linnea-debiasing-premortem-selfserving~.pdf

    • Create a Solid Plan on How to Fail Big This Year: https://www.forbes.com/sites/forbesfinancecouncil/2020/02/07/create-a-solid-plan-on-how-to-fail-big-this-year/

    • Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996/

    • Richard Thaler on X: https://twitter.com/R_Thaler

    • Stewart Butterfield on X: https://twitter.com/stewart

    • Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game)

    • How the Founder of Slack & Flickr Turned Colossal Failures into Billion-Dollar Companies: https://medium.com/swlh/how-the-founder-of-slack-flickr-turned-failures-into-million-and-billion-dollar-companies-7bcaf0d35d66

    • The Most Fascinating Profile You’ll Ever Read About a Guy and His Boring Startup: https://www.wired.com/2014/08/the-most-fascinating-profile-youll-ever-read-about-a-guy-and-his-boring-startup/

    • The Alliance for Decision Education: https://alliancefordecisioneducation.org/

    • Make Better Decisions course on Maven: https://maven.com/annie-duke/make-better-decisions

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Kayvon Beykpour was the longest-serving head of product at Twitter and was GM of Twitter’s consumer division until the platform was acquired by Elon Musk. He originally joined Twitter in 2015 through the acquisition of his company, Periscope, the largest live video streaming platform at the time. Periscope pioneered technology that inspired Instagram Live, TikTok Live, Facebook Live, and other social networks’ expansion into video streaming. In our conversation, we discuss:

    • The story of being let go from Twitter after Elon’s acquisition

    • How he turned Twitter’s stagnant culture around

    • Kayvon’s thoughts on the limitations of frameworks like Jobs to Be Done

    • Why Periscope failed

    • Advice for building consumer products

    • When to copy, when to innovate

    —

    Brought to you by:

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    —

    Find the transcript at: https://www.lennysnewsletter.com/p/twitters-former-head-of-product-kayvon-beykpour

    —

    Where to find Kayvon Beykpour:

    • X: https://twitter.com/kayvz

    • LinkedIn: https://www.linkedin.com/in/kayvz/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Kayvon’s background

    (04:31) Getting Elon up to speed at Twitter

    (11:34) The story of being let go from Twitter after Elon’s acquisition

    (21:09) Changing the product culture at Twitter

    (29:44) Building the “hide replies” feature

    (32:02) Sacred crows, taking bold bets, and reigniting growth

    (34:28) Aquihires and their impact

    (42:40) Tips for successful acquisitions and staffing

    (47:00) The limitations of frameworks like JTBD

    (53:20) Signs you’ve gone too far with a framework

    (57:44) Lessons from building Periscope

    (01:00:41) Reasons why Periscope failed

    (01:07:24) The challenges of implementing video at Twitter

    (01:12:05) Copying ideas in good taste

    (01:17:58) How to get better at building consumer products

    (01:19:51) What Kayvon is building

    (01:20:31) Lightning round

    —

    Referenced:

    • Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/

    • What it’s like to sell your startup for ~$120 million before it’s even launched: Meet Twitter’s new prized possession, Periscope: https://www.businessinsider.com/what-is-periscope-and-why-twitter-bought-it-2015-3

    • Walter Isaacson on LinkedIn: https://www.linkedin.com/in/walter-isaacson-b8b81520/

    • Elon Musk on X: https://twitter.com/elonmusk

    • Parag Agrawal on LinkedIn: https://www.linkedin.com/in/parag-agrawal-5a14742a/

    • Jack Dorsey on LinkedIn: https://www.linkedin.com/in/jack-dorsey-a43b07242/

    • Blackboard: https://en.wikipedia.org/wiki/Blackboard_Inc.

    • Keith Coleman on X: https://twitter.com/kcoleman

    • Esther Crawford on LinkedIn: https://www.linkedin.com/in/esthercrawford/

    • Twitter acquires Chroma Labs: https://tech.hindustantimes.com/tech/news/twitter-acquires-chroma-labs-story-aqvcRPAoYXqXJuAbefA6cN.html

    • John Barnett on LinkedIn: https://www.linkedin.com/in/johnbarnettt/

    • Jobs to Be Done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90

    • Hot takes and techno-optimism from tech’s top power couple: https://www.lennyspodcast.com/hot-takes-and-techno-optimism-from-techs-top-power-couple-sriram-and-aarthi/

    • Nike Is Unveiling the Kobe 11 Tomorrow Using Periscope: https://sneakernews.com/2015/12/13/nike-is-unveiling-the-kobe-11-tomorrow-using-periscope/

    • Chris Sacca’s website: https://chrissacca.com/

    • Facebook Live: https://www.facebook.com/formedia/tools/facebook-live

    • Kevin Hart on X: https://twitter.com/KevinHart4real

    • Clubhouse: https://www.clubhouse.com/

    • Vine: https://en.wikipedia.org/wiki/Vine_(service)

    • Paul Davison on LinkedIn: https://www.linkedin.com/in/davison/

    • Rohan Seth on LinkedIn: https://www.linkedin.com/in/rohanseth/

    • Cryptonomicon: https://www.amazon.com/Cryptonomicon-Neal-Stephenson/dp/0380788624

    • Reamde: https://www.amazon.com/Reamde-Novel-Neal-Stephenson-ebook/dp/B004XVN0WW

    • The Name of the Wind: https://www.amazon.com/Name-Wind-Kingkiller-Chronicle-Book-ebook/dp/B0010SKUYM

    • Star Trek official site: https://www.startrek.com/

    • Dune: part 2: https://www.dunemovie.com/

    • Oppenheimer on Peacock: https://www.peacocktv.com/stream-movies/oppenheimer

    • Tokyo Vice on Max: https://www.max.com/shows/tokyo-vice/e7d93204-7f98-4e62-ab52-6c1da053f942

    • Devs on Hulu: https://www.fxnetworks.com/shows/devs

    • Nick Offerman on X: https://twitter.com/nick_offerman

    • 3 Body Problem on Netflix: https://www.netflix.com/title/81024821

    • Perplexity AI: https://www.perplexity.ai/

    • Particle: https://www.particle.news/

    • Crokinole board game: https://boardgamegeek.com/boardgame/521/crokinole

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Carole Robin spent over 20 years teaching the Stanford Graduate School of Business course Interpersonal Dynamics, affectionately known as “Touchy Feely.” After leaving Stanford, she founded a nonprofit called Leaders in Tech, which applies the Touchy Feely principles to help Silicon Valley executives build their leadership and interpersonal skills. Carole co-authored the popular book Connect: Building Exceptional Relationships with Family, Friends, and Colleagues, which shares key insights from her decades of teaching these courses. In our conversation, we discuss:

    • The benefits of building robust relationships, in life and work

    • The 15% rule, and how it will help you build better relationships

    • The power of vulnerability

    • Examples of how to practice vulnerability

    • Why mental models you build early in life hold you back later

    • The “three realities” and “the net”

    • The art of inquiry

    • Practical tips for avoiding defensiveness when getting feedback

    • The impact of long Covid on Carole’s life

    —

    Brought to you by:

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    —

    Find the transcript at: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

    —

    Where to find Carole Robin:

    • LinkedIn: https://www.linkedin.com/in/carole-robin/

    • Email: [email protected]

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Carole’s background

    (05:17) The importance of building robust relationships

    (10:20) The “Touchy Feely” course at Stanford

    (13:29) An example of the in-class experience

    (17:19) Leaders in Tech: developing interpersonal competence

    (21:36) Progressive disclosure and the 15% rule

    (24:28) Appropriate disclosure

    (26:52) The power of vulnerability

    (34:57) Admitting mistakes and sharing feelings

    (37:08) Understanding mental models

    (42:57) The “three realities” framework

    (53:52) The power of feedback and personal change

    (58:47) The art of inquiry

    (01:03:27) How to get better at giving feedback

    (01:07:47) Exercises and continued learning

    (01:10:49) “Advice hinders relationships”

    (01:16:49) Failure corner: AFOG

    (01:20:30) Takeaways

    (01:21:51) Lessons from long Covid

    —

    Referenced:

    • How to Build Better Relationships: https://www.gsb.stanford.edu/insights/how-build-better-relationships

    • Connect: Building Exceptional Relationships with Family, Friends, and Colleagues: https://www.amazon.com/Connect-Building-Exceptional-Relationships-Colleagues-ebook/dp/B0894279WZ

    • Leaders in Tech: https://leadersintech.org/

    • Leaders in Tech Fellows: https://leadersintech.org/learnaboutfellows

    • Steve Jobs: https://www.forbes.com/profile/steve-jobs/

    • Sheryl Sandberg on X: https://twitter.com/sherylsandberg

    • Ursula Burns: https://www.forbes.com/profile/ursula-burns/

    • Application for Leaders in Tech: https://leadersintech.org/programs-and-applications

    • Vygotsky’s Zone of Proximal Development and Scaffolding Theory: https://www.simplypsychology.org/zone-of-proximal-development.html

    • The Best Leaders Aren’t Afraid to Be Vulnerable: https://hbr.org/2022/07/the-best-leaders-arent-afraid-of-being-vulnerable

    • The Surprising Benefits of Admitting Mistakes: 5 Ways to Build Intellectual Humility: https://www.forbes.com/sites/tracybrower/2021/12/29/the-surprising-benefits-of-admitting-mistakes-5-ways-to-build-intellectual-humility/

    • How to Build Conflict Skills—The Pinch/Crunch Model: https://www.forbes.com/sites/hannahart/2023/12/15/how-to-build-conflict-skills-the-pinchcrunch-model/

    • Slides mentioned (The Three Realities Framework | The 15% Rule | Feedback Guidelines): https://www.notion.so/pen-name/Carole-Robin-on-Lenny-s-Podcast-dc7159208e4242428f4b11ebc92285eb

    • Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322

    • Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey

    • Long COVID: major findings, mechanisms and recommendations: https://www.nature.com/articles/s41579-022-00846-2

    • Leadership, acceptance, and self-management: my journey with long COVID: https://www.linkedin.com/pulse/leadership-acceptance-self-management-my-journey-long-carole-robin/

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Mihika Kapoor is a design-engineer-PM hybrid at Figma, where she was an early PM on FigJam and is now spearheading development on a new product at the company that’s coming out this June. She’s known as the go-to person at Figma for leading new 0-to-1 products, and, as you’ll hear in our conversation, beloved by everyone she works with. Her background includes founding Design Nation, a national nonprofit focused on democratizing design education for undergraduates; spearheading product launches at Meta; and community building within the NYC AI startup scene. In our conversation, we discuss:

    • How to effectively take ideas from 0 to 1 at larger companies

    • How to craft a compelling vision

    • The importance of vulnerability and feedback

    • The role of intuition and product sense in making decisions

    • How to practically communicate your vision

    • How to balance collaboration and strong opinions

    • Advice for building a strong team culture

    • Pivoting with grace and enthusiasm

    • The current AI revolution and its impact on PM

    —

    Brought to you by:

    • Paragon—Ship every SaaS integration your customers want

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    —

    Find the transcript at: https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

    —

    Where to find Mihika Kapoor:

    • X: https://twitter.com/mihikapoor

    • LinkedIn: https://www.linkedin.com/in/mihikakapoor/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Mihika’s background

    (04:29) Core attributes of great product managers

    (07:34) Crafting a compelling vision

    (12:12) The vision behind FigJam

    (18:25) Delivering a vision without design or engineering skills

    (21:52) Creating momentum

    (26:36) The importance of strong conviction

    (27:45) Direct communication

    (32:48) Building hype

    (42:20) Immersing yourself in user insights

    (47:16) Operationalizing user insights

    (50:33) Caring deeply about what you build

    (54:01) Finding passion in your work

    (57:00) Building a strong culture

    (01:07:07) Pivoting with grace and enthusiasm

    (01:11:48) Design Nation

    (01:13:15) Mihika’s weaknesses

    (01:16:07) Building new products at larger companies

    (01:20:50) Coming up with a great idea

    (01:22:49) The key to going from 0 to 1

    (01:26:47) Spreading the idea across the company

    (01:29:15) Closing thoughts

    (01:32:11) Lightning round

    —

    Referenced:

    • Figma: https://www.figma.com/

    • Sho Kuwamoto on LinkedIn: https://www.linkedin.com/in/shokuwamoto/

    • The Medici Effect: What Elephants and Epidemics Can Teach Us About Innovation: https://www.amazon.com/Medici-Effect-Preface-Discussion-Guide/dp/1633692949

    • FigJam: https://www.figma.com/figjam/

    • Cognition: https://www.cognition-labs.com/

    • Devin: https://www.cognition-labs.com/introducing-devin

    • David Hoang on LinkedIn: https://www.linkedin.com/in/dhoang2/

    • Replit: https://replit.com/

    • The Making of Maker Week at Figma: https://www.figma.com/blog/the-making-of-maker-week/

    • Yuhki Yamashita on LinkedIn: https://www.linkedin.com/in/yuhki/

    • Jeff Bezos’ Simple Decision-Making Framework Will Give You Clarity, Conviction, and Courage: https://medium.com/illumination/jeff-bezos-simple-decision-making-framework-will-give-you-clarity-conviction-and-courage-adf8d0183625

    • Alice Ching on LinkedIn: https://www.linkedin.com/in/aliceching/

    • Karl Jiang on LinkedIn: https://www.linkedin.com/in/karl-jiang-4a07424/

    • Kris Rasmussen on LinkedIn: https://www.linkedin.com/in/kristopherrasmussen/

    • Config: https://config.figma.com/

    • Dev Mode: https://www.figma.com/dev-mode/

    • Asana: https://asana.com/

    • Julie Zhuo on LinkedIn: https://www.linkedin.com/in/julie-zhuo/

    • StrengthsFinder test: https://www.gyfted.me/personality-quiz/strengthsfinder-test-free

    • Dylan Field on LinkedIn: https://www.linkedin.com/in/dylanfield/

    • Vishal Shah on LinkedIn: https://www.linkedin.com/in/vishalnshah/

    • Design Disruptors: https://www.invisionapp.com/films/design-disruptors

    • Daniel Burka on LinkedIn: https://www.linkedin.com/in/dburka/

    • Jamie Myrold on LinkedIn: https://www.linkedin.com/in/jamiemyrold/

    • Design Nation: https://dn.businesstoday.org/

    • Stuart Weitzman on X: https://twitter.com/StuartWeitzman

    • Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/

    • Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennyspodcast.com/building-a-long-and-meaningful-career-nikhyl-singhal-meta-google/

    • Jambot: https://www.figma.com/community/widget/1274481464484630971/jambot

    • Hestia: https://en.wikipedia.org/wiki/Hestia

    • Harry Potter series: https://www.amazon.com/Harry-Potter-Paperback-Box-Books/dp/0545162076

    • Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927/

    • Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649

    • The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X

    • Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx

    • Dune on Max: https://www.max.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7

    • Dune: Part 2: https://www.dunemovie.com/

    • Arc browser: https://arc.net/

    • Pika: https://pika.art/home

    • The power of recognition: Why you should celebrate your employees | Josh Miller: https://www.lennyspodcast.com/videos/the-power-of-recognition-why-you-should-celebrate-your-employees-josh-miller/

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Dalton Caldwell is Managing Director and Group Partner at Y Combinator. Prior to YC, he was the co-founder and CEO of imeem (acquired by MySpace in 2009) and the co-founder and CEO of App.net. During his time at YC, he’s advised more than 35 YC unicorns, including DoorDash, Amplitude, Webflow, and Retool, and has worked across 21 different YC batches. He’s also racked up more than 6,500 office hours with founders. In our conversation, we discuss:

    • Why founders need to adopt the mindset “Just don’t die”

    • The most common reason startups fail

    • When to pivot, and characteristics of a good pivot

    • The concept of “tar pit ideas” and examples of bad startup ideas

    • Why investors say no to startups

    • The importance of market size in investment decisions

    • The pitfalls of founders over-delegating

    • Effective ways to talk to customers

    • 20 ideas Dalton is looking to fund

    —

    Brought to you by:

    • Eppo—Run reliable, impactful experiments

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    • Coda—The all-in-one collaborative workspace

    —

    Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups

    —

    Where to find Dalton Caldwell:

    • X: https://twitter.com/daltonc

    • LinkedIn: https://www.linkedin.com/in/daltoncaldwell/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Dalton’s background

    (04:41) The value of simple advice

    (07:04) Dalton’s advice: “Just don’t die”

    (08:39) Knowing when to stop

    (11:45) Deciding to pivot

    (14:26) Characteristics of a good pivot

    (17:53) Knowing when to pivot

    (19:03) Zip’s journey and finding a market

    (21:22) Why Dalton says to “Move towards the mountains and the desert”

    (23:45) Tar pit ideas

    (26:49) Understanding why investors say no

    (29:14) The importance of market size

    (32:16) Avoiding over-delegation and hiring senior people too early

    (36:43) Why startups fail

    (40:30) Effectively talking to customers

    (45:17) Examples of startups hustling to talk to customers

    (48:01) Patterns of successful startups

    (52:05) YC’s Request for Startups

    (55:37) Early days of Silicon Valley

    (01:05:33) Contrarian corner: growth hacking for early startups

    (01:09:28) Failure corner

    (01:11:15) Closing thoughts

    (01:12:22) Lightning round

    —

    Referenced:

    • Y Combinator: https://www.ycombinator.com/

    • Tiger Woods’s website: https://tigerwoods.com/

    • Co-Founder Mistakes That Kill Companies & How to Avoid Them: https://www.youtube.com/watch?v=dlfjs_eEEzs

    • Daniel Alberson’s LinkedIn post about Y Combinator: https://www.linkedin.com/posts/alberson_i-left-my-dream-job-as-a-product-manager-activity-7089677882431533056-jJ9H

    • Companies in Y Combinator W17 Batch: https://www.ycdb.co/batch/w17

    • Brex: https://www.brex.com/

    • Retool: https://retool.com/

    • Segment: https://segment.com/

    • Mixpanel: https://mixpanel.com/

    • Whatnot: https://www.whatnot.com/

    • Andreessen Horowitz: https://a16z.com/

    • Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/

    • Rujul Zaparde on LinkedIn: https://www.linkedin.com/in/rujulz/

    • Zip: https://ziphq.com/

    • Lu Cheng on LinkedIn: https://www.linkedin.com/in/lu-cheng-973b7830/

    • Avoid these tempting startup tar pit ideas: https://www.ycombinator.com/library/Ij-avoid-these-tempting-startup-tarpit-ideas

    • Airbnb acquires Localmind to create crowdsourced advice about neighborhoods: https://skift.com/2012/12/13/airbnb-acquires-localmind-to-create-crowdsourced-advice-about-neighborhoods/

    • Foursquare: https://foursquare.com/

    • Razorpay: https://razorpay.com/

    • Total Addressable Market: https://www.productplan.com/glossary/total-addressable-market/

    • Lenny Bogdonoff on LinkedIn: https://www.linkedin.com/in/rememberlenny/

    • Milk Video: https://milkvideo.com/

    • Lessons from working with 600+ YC startups | Gustaf Alströmer (Y Combinator, Airbnb): https://www.lennyspodcast.com/lessons-from-working-with-600-yc-startups-gustaf-alstromer-y-combinator-airbnb/

    • How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups

    • Collison installation: https://news.ycombinator.com/item?id=18400504

    • Stripe: https://stripe.com/

    • Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/

    • John Collison on LinkedIn: https://www.linkedin.com/in/johnbcollison/

    • Tony Xu on LinkedIn: https://www.linkedin.com/in/xutony/

    • Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine/

    • Ryan Petersen on LinkedIn: https://www.linkedin.com/in/rpetersen/

    • Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/

    • YC’s latest Request for Startups: https://www.ycombinator.com/blog/ycs-latest-request-for-startups

    • ERPs: https://www.ycombinator.com/rfs#new-enterprise-resource-planning-software

    • Commercial open source companies: https://www.ycombinator.com/rfs#commercial-open-source-companies

    • New space companies: https://www.ycombinator.com/rfs#new-space-companies

    • A way to end cancer: https://www.ycombinator.com/rfs#a-way-to-end-cancer

    • Spatial computing: https://www.ycombinator.com/rfs#spatial-computing

    • New defense technology: https://www.ycombinator.com/rfs#new-defense-technology

    • Bringing manufacturing back to America: https://www.ycombinator.com/rfs#bring-manufacturing-back-to-america

    • Better enterprise glue: https://www.ycombinator.com/rfs#better-enterprise-glue

    • Small fine-tuned models, as an alternative to giant generic ones: https://www.ycombinator.com/rfs#small-finetuned-models-as-an-alternative-to-giant-generic-ones

    • Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

    • Sam Altman on X: https://twitter.com/sama

    • Sean Parker on LinkedIn: https://www.linkedin.com/in/parkersean/

    • Owen Van Natta on LinkedIn: https://www.linkedin.com/in/owen-van-natta-444a7/

    • Marc Andreessen on X: https://twitter.com/pmarca

    • Picplz 1, Instagram 0 as VC firm Andreessen Horowitz chooses photo app rival: https://www.reuters.com/article/idUS2587232395/

    • Gustaf Alstromer—How to Get Users and Grow: https://www.youtube.com/watch?v=T9ikpoF2GH0

    • Getting to Yes: Negotiating Agreement Without Giving In: https://www.amazon.com/Getting-Yes-Negotiating-Agreement-Without/dp/0143118757

    • Founding Sales: The Early Stage Go-to-Market Handbook: https://www.amazon.com/Founding-Sales-Go-Market-Handbook-ebook/dp/B08PMK17Z1

    • Founder-led sales | Pete Kazanjy (Founding Sales, Atrium): https://www.lennyspodcast.com/founder-led-sales-pete-kazanjy-founding-sales-atrium/

    • The Sopranos on HBO: https://www.hbo.com/the-sopranos

    • The Wire on HBO: https://www.hbo.com/the-wire

    • Columbo on Prime Video: https://www.amazon.com/Columbo-Season-1/dp/B008SA89HA

    • Oura ring: https://ouraring.com/

    • Apple watch: https://www.apple.com/watch/

    • SiPhox: https://siphoxhealth.com/

    • Dalton & Michael on YouTube: https://www.youtube.com/playlist?list=PLQ-uHSnFig5Nd98Sc9I-kkc0ZWe8peRMC

    • How Future Billionaires Get Sh*t Done: https://www.youtube.com/watch?v=ephzgxgOjR0

    • The Student’s Guide to Becoming a Successful Startup Founder: https://www.youtube.com/watch?v=O5KCB2p6SB8

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • David DeSanto is the chief product officer of GitLab, which is the largest remote-only company in the world. They share many of their team meetings on YouTube, and they’ve grown from being an open-source code management product competing with GitHub to a multi-product platform that covers security, compliance, continuous integration, project management, and deployment tools, many of which are infused with AI magic. In our conversation, we discuss:

    • How GitLab operationalizes transparency

    • The philosophy behind recording and sharing team meetings on YouTube

    • Their extensive public employee handbook

    • GitLab’s core value of having “short toes”

    • Challenges and advice for doing remote work well

    • Strategies for ensuring effective communication in a remote work environment

    • GitLab’s breadth-over-depth strategy

    • The company’s unique approach to AI

    • The value of using humor in high-stakes conversations

    —

    Brought to you by:

    • Orb—The flexible billing engine for modern pricing

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    • Paragon—Ship every SaaS integration your customers want

    —

    Find the transcript at: https://www.lennysnewsletter.com/p/the-gitlab-way

    —

    Where to find David DeSanto:

    • X: https://twitter.com/david_desanto

    • LinkedIn: https://www.linkedin.com/in/ddesanto/

    • Threads: https://www.threads.net/@david.the.beard

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) David’s background

    (04:20) Maintaining an epic beard

    (05:29) Why GitLab publicly shares team meetings

    (09:49) The GitLab Handbook

    (11:30) GitLab’s issue tracker

    (14:29) How to successfully build a culture of transparency

    (18:11) Benefits of operating with transparency

    (19:55) The value of building in public

    (21:53) How GitLab implements their core value of kindness

    (25:16) What it means to have “short toes”

    (27:41) Other core values

    (32:16) Common reasons for not fitting in at GitLab

    (34:42) Advice for remote teams

    (42:04) Advice for getting into product

    (43:52) Advice for PMs who are struggling in a remote world

    (48:25) Specific tools that help with remote work

    (53:13) Time zones and remote work

    (57:18) Breadth-over-depth strategy

    (01:04:14) AI at GitLab

    (01:13:11) GitLab’s products and solutions

    (01:14:54) Lightning round

    —

    Referenced:

    • GitLab: https://about.gitlab.com/

    • UX Showcase—David DeSanto introduction to UX team and AMA: https://www.youtube.com/watch?v=fEdsmnVKNj4

    • The GitLab Handbook: https://handbook.gitlab.com/

    • Sid Sijbrandij on LinkedIn: https://www.linkedin.com/in/sijbrandij/

    • Y Combinator: https://www.ycombinator.com/

    • GitLab issues: https://docs.gitlab.com/ee/user/project/issues/

    • Salesforce: https://www.salesforce.com/

    • GitLab values: https://handbook.gitlab.com/handbook/values

    • GitLab organizational structure: https://handbook.gitlab.com/handbook/company/structure

    • GitLab direction: https://about.gitlab.com/direction/

    • Dogfooding: A simple practice to help you build better products: https://medium.com/agileinsider/dogfooding-a-simple-practice-to-help-you-build-better-products-b5954af4d5f7

    • The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-adding-a-plg

    • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

    • HubSpot: https://www.hubspot.com/

    • Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986

    • Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennyspodcast.com/geoffrey-moore-on-finding-your-beachhead-crossing-the-chasm-and-dominating-a-market/

    • Open-core model: https://en.wikipedia.org/wiki/Open-core_model

    • GitLab Duo: https://about.gitlab.com/gitlab-duo/

    • GitLab Docs: https://docs.gitlab.com/

    • Anthropic: https://www.anthropic.com/

    • GitLab Acquires UnReview to Expand Its DevOps Platform with Machine Learning Capabilities: https://about.gitlab.com/press/releases/2021-06-02-gitlab-acquires-unreview-machine-learning-capabilities/

    • Essentialism: The Disciplined Pursuit of Less: https://www.amazon.com/Essentialism-Disciplined-Pursuit-Greg-McKeown/dp/0804137382

    • The Mission Critical Core/Context Model for Product Managers: https://secretpmhandbook.com/the-mission-critical-corecontext-model-for-product-managers/

    • The Devil’s Hour on AppleTV+: https://tv.apple.com/us/show/the-devils-hour/umc.cmc.3zw4tyzd4lvor5mwhujms63x3

    • Glass Onion: A Knives Out Mystery on Netflix: https://www.netflix.com/title/81458416

    • Taylor Swift’s The Eras Tour on Prime Video: https://www.amazon.com/TAYLOR-SWIFT-ERAS-EXTENDED-VERSION/dp/B0CP99SN2B

    • The STAR method: https://capd.mit.edu/resources/the-star-method-for-behavioral-interviews/

    • Artifact News: https://artifact.news/

    • Superhuman: https://superhuman.com/

    • Arc browser: https://arc.net/

    • An inside look at how The Browser Company builds product: https://www.lennysnewsletter.com/p/competing-with-giants-an-inside-look

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
  • Todd Jackson is a Partner at First Round Capital. Before moving into venture capital, he played a crucial role as VP of Product and Design at Dropbox, guiding the company until its IPO in 2018. Prior to Dropbox, Todd led product management for Twitter’s Content and Discovery teams after selling his startup, Cover, to Twitter in 2014. Before Cover, Todd oversaw product development for Facebook’s Newsfeed, Photos, and Groups. He kickstarted his career at Google as an associate product manager and eventually led product for Gmail, witnessing its growth from beta to 200 million users. In our conversation, we discuss:

    • Why product-market fit (PMF) matters

    • First Round Capital’s four-part PMF framework

    • Level one: Nascent product-market fit

    • Level two: Developing product-market fit

    • Level three: Strong product-market fit

    • Level four: Extreme product-market fit

    • Examples of companies at each level

    • How to know if you’re stuck at a level, and how to get unstuck

    • What to change if you’re stuck: persona, problem, promise, and product

    • The goals and challenges at each stage

    —

    Brought to you by:

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    —

    Find the full transcript at: https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

    —

    Where to find Todd Jackson:

    • X: https://twitter.com/tjack

    • LinkedIn: https://www.linkedin.com/in/toddj0/

    —

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    —

    In this episode, we cover:

    (00:00) Todd’s background

    (06:07) First Round Capital’s PMF framework

    (09:07) Why product-market fit is so important

    (11:02) Who can benefit from this framework

    (12:55) The product-market fit method

    (16:54) Broad overview of the framework

    (21:35) Level one: nascent product-market fit

    (33:16) The four P’s

    (39:13) Level two: developing product-market fit

    (49:13) Signs you’re stuck at level two, and what to do

    (55:12) Level three: strong product-market fit

    (01:00:17) Signs you’re stuck at level three, and what to do

    (01:02:22) Level four: extreme product-market fit

    (01:06:55) Rough timelines for each level

    (01:11:18) A quick recap of the framework

    (01:12:15) Diving deeper on the four P’s: what to do if you’re stuck

    (01:13:56) Dollar-driven discovery

    (01:25:11) Apply for the product-market-fit method program

    —

    Referenced:

    • First Round: https://firstround.com/

    • Twitter Acquires Cover: https://www.vox.com/2014/4/7/11625332/twitter-acquires-cover-an-android-mobile-startup

    • Dropbox: https://www.dropbox.com/

    • Rahul Vohra on LinkedIn: https://www.linkedin.com/in/rahulvohra/

    • How Superhuman Built an Engine to Find Product Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/

    • How to validate your startup idea: https://www.lennysnewsletter.com/p/validating-your-startup-idea

    • How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups

    • How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket

    • A guide for finding product-market fit in B2B: https://www.lennysnewsletter.com/p/finding-product-market-fit

    • Product-market fit method: http://pmf.firstround.com/

    • Stripe: https://stripe.com/

    • Plaid: https://plaid.com/

    • Paths to PMF: https://review.firstround.com/series/product-market-fit/

    • WeWork: https://www.wework.com/

    • Casper: https://casper.com/

    • Vanta: https://www.vanta.com/

    • Christina Cacioppo on LinkedIn: https://www.linkedin.com/in/ccacioppo/

    • Ramp: https://ramp.com/

    • Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennyspodcast.com/velocity-over-everything-how-ramp-became-the-fastest-growing-saas-startup-of-all-time-geoff-charl/

    • Jack Altman on LinkedIn: https://www.linkedin.com/in/jackealtman/

    • Lattice: https://lattice.com/

    • Zachary Perret on LinkedIn: https://www.linkedin.com/in/zperret/

    • Positioning: https://www.lennysnewsletter.com/p/positioning

    • Retool: https://retool.com/

    • David Hsu on LinkedIn: https://www.linkedin.com/in/dvdhsu/

    • Persona: https://withpersona.com/

    • Rick Song on LinkedIn: https://www.linkedin.com/in/rick-song-25198b24/

    • Lloyd Tabb on LinkedIn: https://www.linkedin.com/in/lloydtabb/

    • Looker: https://en.wikipedia.org/wiki/Looker_(company)

    • Jason Boehmig on LinkedIn: https://www.linkedin.com/in/jboehmig/

    • Ironclad: https://ironcladapp.com/

    • Lessons in leadership | Scaling an org and tactical management advice | Jack Altman (Lattice): https://www.youtube.com/watch?v=cZzXqf61mrQ

    • Filip Kaliszan on LinkedIn: https://www.linkedin.com/in/kaliszan/

    • Verkada: https://www.verkada.com/

    • Ali Ghodsi on LinkedIn: https://www.linkedin.com/in/alighodsi/

    • Databricks: https://www.databricks.com/

    • Stripe Radar: https://stripe.com/radar

    • Stripe Atlas: https://stripe.com/atlas

    • Square Stand: https://squareup.com/shop/hardware/us/en/products/ipad-pos-stand-integrated-card-reader

    • Cash App: https://cash.app/

    • Square Checking: https://squareup.com/us/en/campaign/banking/checking

    • Square Loan: https://squareup.com/help/us/en/article/5654-get-started-with-square-capital

    • Casey Winters on LinkedIn: https://www.linkedin.com/in/caseywinters/

    • How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennyspodcast.com/how-to-sell-your-ideas-and-rise-within-your-company-casey-winters-eventbrite/

    • Josh Kopelman on LinkedIn: https://www.linkedin.com/in/jkopelman/

    • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennyspodcast.com/videos/the-art-and-science-of-pricing-madhavan-ramanujam-monetizing-innovation-simon-kucher/

    • Simon Kucher: https://www.simon-kucher.com/

    —

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

    —

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe